(E)-3,7-二甲基-2,6-辛二烯醛 | 141-27-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (E)-3,7-二甲基-2,6-辛二烯醛
• 中文别名: (2Z)-3,7-二甲基-2,6-辛二烯醛(Z)-柠檬醛
• 英文名称: 3,7-dimethyl-2,6-octadienal
• 英文别名: Geranial；α-citral；citral；(E)-citral；(E)-3,7-dimethylocta-2,6-dienal；trans-citral；3,7‐dimethylocta‐2,6‐dienal；(2E)-3,7-dimethylocta-2,6-dienal；(E)-3,7-dimethyl-2,6-octadienal；3,7-dimethyl-(E)-2,6-octadienal
• CAS: 141-27-5
• 化学式: C₁₀H₁₆O
• mdl: MFCD00006997
• 分子量: 152.236
• InChiKey: WTEVQBCEXWBHNA-JXMROGBWSA-N

物化性质

• 沸点：
  bp2.6 92-93°
• 密度：
  d420 0.8888
• 溶解度：
  可溶于氯仿（少许）、乙醇（少许）
• LogP：
  2.76-3.445 at 25℃
• 物理描述：
  Citral appears as a clear yellow colored liquid with a lemon-like odor. Less dense than water and insoluble in water. Toxic by ingestion. Used to make other chemicals.
• 颜色/状态：
  Mobile pale yellow liquid
• 气味：
  Strong lemon odor
• 味道：
  Taste threshold values: Detection: 28 to 120 ppb; alpha-citral, 32 to 460 ppb; beta-citral, 30 to 460 ppb.
• 熔点：
  Melting point <-10 °C.
• 闪点：
  195 °F (91 °C) (CLOSED CUP)
• 蒸汽密度：
  Relative vapor density (air = 1): 5.3
• 蒸汽压力：
  9.13X10-2 mm Hg at 25 °C (est)
• 稳定性/保质期：
  1. 存在于烟叶中。 2. 存在于柠檬草油、柠檬油、山苍子油等中。 3. 具有较强的化学活性。
• 自燃温度：
  225 °C
• 分解：
  When heated to decomposition it emits acrid smoke and irritating fumes.
• 气味阈值：
  Aroma threshold values: Detection: 28 to 120 ppb; alpha-citral, 32 to 460 ppb; beta citral, 30 to 460 ppb.
• 折光率：
  Index of refraction = 1.4860-1.4900 at 20 °C, not optically active
• 保留指数：
  1249;1250;1240;1239;1244;1268;1275;1244;1241;1241;1268;1246;1262;1249;1260;1223;1224.5;1249;1252;1252

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

Citral ... 在实验动物中 ... 部分转化为所谓的Hildebrandt酸，其中发生了双键欧米伽氧化。

Citral ... in experimental animals ... is converted in part to the so-called Hildebrandt acid in which a double omega oxidation has taken place.

来源:Hazardous Substances Data Bank (HSDB)

代谢

香叶醛是一种天然存在的萜烯系列脂肪醛，是橙花醛和柠檬醛的同分异构体混合物。在本研究中，对雄性F344大鼠尿液中香叶醛的代谢物进行了表征。研究了香叶醛在C-8甲基位置的对映选择性氧化，以及胆汁和尿液代谢物的水解敏感性。为了识别代谢物，在大鼠单次口服500毫克/千克剂量的(14)C香叶醛后，通过干冰收集24小时内的尿液。尿液中的消除是迅速的，大约有50%的剂量在24小时内被排泄。香叶醛被迅速代谢并以代谢物的形式排出，包括几种酸和一种胆汁葡萄糖苷酸。分离并鉴定了7种尿液代谢物：3-羟基-3,7-二甲基-6-辛二酸；3,8-二羟基-3,7-二甲基-6-辛二醇酸；3,9-二羟基-3,7-二甲基-6-辛二醇酸；E-和Z-3,7-二甲基-2,6-辛二烯二酸；3,7-二甲基-6-辛二酸；E-3,7-二甲基-2,6-辛二烯酸。尽管香叶醛是一种α,β-不饱和醛，具有潜在的活性，但香叶醛的尿液代谢物似乎来源于除了与双键进行亲核加成以外的代谢途径。

Citral is a naturally occurring aliphatic aldehyde of the terpene series and is an isomeric mixture of geranial and neral. In this study, urinary metabolites of citral in male F344 rats were characterized. Stereospecific oxidation of citral at the C-8 methyl was investigated, as was the hydrolytic sensitivity of biliary and urinary metabolites. For metabolite identification, urine was collected over dry ice for 24 hr after a single po 500 mg/kg dose of (l4)C citral. Elimination in urine was rapid, with approximately 50% of the dose excreted within 24 hr. Citral was rapidly metabolized and excreted as metabolites, including several acids and a biliary glucuronide. Seven urinary metabolites were isolated and identified: 3-hydroxy-3,7-dimethyl-6-octenedioic acid; 3,8-dihydroxy-3,7-dimethyl-6-octenolc acid; 3,9-dihydroxy-3,7-dimethyl-6-octenolc acid; E- and Z-3,7-dimethyl-2,6-octadienedioic acid; 3,7-dimethyl-6-octenedioic acid; and E-3,7-dimethyl-2,6-octadienoic acid. Although citral is an alpha,beta-unsaturated aldehyde and has the potential of being reactive, the urinary metabolites of citral appear to arise from metabolic pathways other than nucleophilic addition to the double bond.

来源:Hazardous Substances Data Bank (HSDB)

代谢

柠檬醛的体内代谢报告表明，主要的代谢途径是将其转化为相应的酸，可能是通过醛脱氢酶。在当前研究中，从雄性Sprague-Dawley大鼠中制备了肝线粒体和细胞质组分，以评估柠檬醛的体外代谢。在任一亚细胞组分中均未观察到醛脱氢酶介导的柠檬醛氧化证据。相反，发现柠檬醛是低KM线粒体形式的醛脱氢酶对乙醛氧化的强抑制剂。在柠檬醛存在下测量这种同工酶的体外乙醛氧化率，估计出Ki为360 nM。观察到柠檬醛在细胞质组分中很容易被酒精脱氢酶还原为相应的醇。在NADH存在下，柠檬醛的还原以两个不同的速率进行。柠檬醛的不同醇脱氢酶介导还原速率可能是由于两种柠檬醛异构体，即香叶醛（反式）和橙花醛（顺式）对酶的不同亲和力所致。

Reports of the in vivo metabolism of citral suggest that a primary route of metabolism is conversion to the corresponding acid presumably by aldehyde dehydrogenases. In the present study, hepatic mitochondrial and cytosolic fractions were prepared from male Sprague-Dawley rats to assess in vitro metabolism of citral. Evidence of aldehyde dehydrogenases-mediated citral oxidation was not seen in either subcellular fraction. On the contrary, citral was found to be a potent inhibitor of acetaldehyde oxidation by the low-KM mitochondrial form of aldehyde dehydrogenases. Measurement of the in vitro acetaldehyde oxidation rates of this isozyme in the presence of citral lead to the estimation of a Ki of 360 nM. It was observed that citral was readily reduced to the corresponding alcohol by alcohol dehydrogenase in the cytosolic fraction. The reduction of citral in the presence of NADH proceeded at two distinct rates. It is possible that the differential alcohol dehydrogenase-mediated reduction rates of citral are the result of varying affinities for the enzyme of two citral, isomers, geranial (trans) and neral (cis).

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

香叶醇从胃肠道被迅速吸收。由于香叶醇具有极高的挥发性，因此大部分通过皮肤应用的剂量会因挥发而损失，但留在皮肤上的香叶醇吸收得相当好。香叶醇被迅速代谢并以代谢物的形式排出。尿液是主要的排出途径。这种化学物质在啮齿动物中的急性毒性较低，因为口服或皮肤的LD50值超过1000 mg/kg。在大白兔中，这种化学物质对皮肤有刺激性，但对眼睛无刺激性。有证据表明，这种化学物质对人类皮肤有致敏作用。几项重复口服剂量的研究表明，在每天接触剂量低于1000 mg/kg时，香叶醇没有不良影响，而在超过1000 mg/kg/day的剂量下，鼻腔或前胃（首次接触部位）可能出现一些组织学变化，这可能是由于刺激所致。F344/N大鼠（雄性和雌性）在饲料中接受微囊化香叶醇，浓度为0、0.63、1.25、2.5、5和10%（相应剂量：0、142、285、570、1140和2280 mg/kg/day），持续14天。在没有炎症反应的情况下，在1140和2280 mg/kg/day的剂量下，观察到鼻咽部呼吸上皮的轻度至中度增生和/或鳞状化生。NOAEL（无观察到不良效应的剂量）确定为570 mg/kg/day。在一项OECD初步生殖毒性筛选试验[TG 421]中，将香叶醇通过灌胃给予Crj:CD(SD)大鼠，雄性剂量为0、40、200和1000 mg/kg/day，持续46天，雌性剂量为39-50天，包括交配和妊娠期，直到哺乳期第3天。在没有炎症反应的情况下，在1140和2280 mg/kg/day的剂量下，观察到鼻咽部呼吸上皮的轻度至中度增生和/或鳞状化生。NOAEL（无观察到不良效应的剂量）确定为570 mg/kg/day。在一项OECD初步生殖毒性筛选试验[TG 421]中，将香叶醇通过灌胃给予Crj:CD(SD)大鼠，雄性剂量为0、40、200和1000 mg/kg/day，持续46天，雌性剂量为39-50天，包括交配和妊娠期，直到哺乳期第3天。在1000 mg/kg/day的剂量下，观察到前胃的鳞状增生、溃疡和肉芽肿形成。因此，重复剂量的毒性NOAEL为200 mg/kg/day。上述初步生殖研究中的生殖毒性，没有检测到对两性的生殖能力、器官重量或生殖器官的组织病理学的影响，以及分娩或母性行为的影响。然而，在1000 mg/kg组中，雄性和雌性幼崽的体重减轻。因此，口服发育毒性的NOAEL为200 mg/kg/day。在一项致畸性研究中，将SD孕鼠在妊娠第6-15天每天吸入6小时的香叶醇，平均浓度为0、10或34 ppm的蒸气，或68 ppm的气溶胶/蒸气混合物。即使在母体效应的存在下，68 ppm时也没有显著的致畸性。确定了吸入致畸性的NOAEL为68 ppm（423 mg/m3）。七项细菌反向突变研究显示，无论有无代谢激活，结果均为阴性。对于非细菌体外研究，中国仓鼠细胞的两项染色体畸变结果为阴性，然而在同一细胞中，一项姐妹染色单体交换的结果为阳性。此外，两项啮齿动物的体内微核试验结果为阴性。根据上述信息，香叶醇的遗传毒性潜力可以认为是阴性。NTP（美国国家毒理学计划）研究表明，在雄性和雌性大鼠以及雄性小鼠中没有发现致癌活性的证据，但在雌性小鼠中发现了恶性淋巴瘤的证据（大鼠饲料中最高可达4000 ppm，小鼠饲料中最高可达2000 ppm）。只有某些大鼠品系的皮肤应用香叶醇会诱导前列腺增生，但严重程度较低。然而，在大鼠和小鼠的NTP口服致癌性研究中，没有在任何雄性生殖器官（包括前列腺）发现病变（肿瘤性或非肿瘤性）。由于大鼠皮肤研究中发现的效应在不同品系之间存在显著差异，且这些工作主要在一个实验室进行，因此这些效应的健康意义尚不确定。

Citral was rapidly absorbed from the gastro -intestinal tract. Much of an applied dermal dose was lost due to its extreme volatility, but the citral remaining on the skin was fairly well absorbed. Citral was rapidly metabolized and excreted as metabolites. Urine was the major route of elimination. Acute toxicity of this chemical is low in rodents because the oral or dermal LD50 values were more than 1000 mg/kg. This chemical is irritating to skin and not irritating to eyes in rabbits. There is some evidence that this chemical is a human skin sensitizer. Several repeated dose oral studies show no adverse effect of citral at less than 1,000 mg/kg/day exposure and some histological changes in the nasal cavity or forestomach, the first exposure sites, probably due to irritation, at more than 1,000 mg/kg/day. Male and female F344/N rats received microencapsulated citral in feed at concentrations of 0, 0.63, 1.25, 2.5, 5 and 10% (resultant doses: 0, 142, 285, 570, 1,140 and 2,280 mg/kg/day) for 14 days. Minimal to mild hyperplasia and/or squamous metaplasia of the respiratory epithelium was observed in nasal cavity without inflammatory response at 1,140 and 2,280 mg/kg/day of both sexes. The NOAEL was established at 570 mg/kg/day. In an OECD preliminary reproduction toxicity screening test [TG 421], citral was administered to Crj:CD (SD) rats by gavage at doses of 0, 40, 200 and 1,000 mg/kg/day in males for 46 days and in females for 39- 50 days including before and through mating and gestation periods and until day 3 of lactation. Squamous hyperplasia, ulcer and granulation in lamina propria were observed in the forestomach at 1,000 mg/kg/day of both sexes. Therefore, the NOAEL for repeated dose toxicity was 200 mg/kg/day for both sexes. As for reproductive toxicity in the above preliminary reproductive study, no effects were detected in reproductive ability, organ weights or histopathology of the reproductive organs of both sexes, and delivery or maternal behavior. However, body weights of male and female pups were reduced in the 1000 mg/kg group. Therefore, an oral NOAEL for developmental toxicity was 200 mg/kg/day. In a teratogenicity study, SD pregnant rats were exposed to citral by inhalation for 6 hr/day on gestation days 6-15 at mean concentration of 0, 10 or 34 ppm as vapour, or 68 ppm as an aerosol/vapour mixture. Even in the presence of the maternal effects, no significant teratogenicity was noted at 68 ppm. An inhalation NOAEL of teratogenicity was established at 68 ppm (423 mg/m3). Seven bacterial reverse mutation studies indicate negative results with and without metabolic activation. As for non-bacterial in vitro study, two chromosomal aberration results in Chinese hamster cells are negative however one positive result in sister chromatid exchange is given in the same cells. Add itionally, two in vivo micronucleus tests in rodents indicate negative results. Based on the above information, the genotoxic potential of citral can be considered to be negative. A NTP study shows that there was no evidence of carcinogenic activity in male/female rats and male mice but some evidence of malignant lymphoma in female mice (up to 4,000 ppm in feed in rats and up to 2,000 ppm in feed in mice). Dermal application of citral induces prostate hyperplasia with low severity only in some strains of rats. However, the NTP oral carcinogenicity studies in rats and mice found no evidence of lesions (neoplastic or non-neoplastic) in any male reproductive organ, including the prostate. The health significance of the effects seen in the dermal studies in rats is uncertain due to dramatic strain differences and it is noted that the work has primarily been performed in a single laboratory.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 吸入症状

咳嗽。

Cough.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 皮肤症状

红色。

Redness.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 副作用

职业性肝毒素 - 第二性肝毒素：在职业环境中的毒性效应潜力是基于人类摄入或动物实验的中毒案例。 皮肤致敏剂 - 可以诱导皮肤过敏反应的制剂。 ACGIH致癌物 - 无法分类。

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. Skin Sensitizer - An agent that can induce an allergic reaction in the skin. ACGIH Carcinogen - Not Classifiable.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 相互作用

本研究旨在分析免疫调节化合物完全弗氏佐剂（CFA）和环孢素A（CsA）单独使用或与柠檬醛一起使用对大鼠前列腺增生的诱导和程度的影响。将未成年Wistar大鼠（42天大）单独给予柠檬醛或与CFA或CsA联合使用一个月。使用组织评分协议对增生性病变的程度进行半定量分析。CsA并未诱导增生性变化，也未消除柠檬醛促进增生变化的能力，也未影响间质中淋巴细胞的渗出程度。然而，CFA本身对前列腺上皮细胞具有增殖作用，并且增强了柠檬醛诱导的增生性变化，甚至诱导了腺上皮细胞的非典型转化。

... The aim of the present study was to analyze the effect of the immunomodulator compounds, Complete Freund Adjuvant (CFA) and cyclosporin A (CsA), administered alone or together with citral on the induction and extent of rat prostatic hyperplasia. Adolescent Wistar rats (42 days old) were given citral alone or combined with CFA or CsA for one month. Semiquantitative analysis of the extent of the hyperplastic lesions was made with the histoscore protocol. CsA did not induce hyperplastic changes or abolish the ability of citral to promote hyperplastic changes or to affect the extent of the lymphocytic exudate in the stroma. CFA itself, however, had a proliferative action on the prostatic epithelium, and it augmented the hyperplastic changes induced by citral and even induced atypical transformations of the acinar epithelium.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

F344雄性大鼠单次口服5、50或500毫克/千克体重或静脉注射5毫克/千克体重的14C标记在C1和C2位的柠檬醛。72小时后，处死动物并分析组织和排泄物中的放射性。大部分放射性标记在24小时内以14CO2或[14C]柠檬醛的形式通过尿液、粪便和呼出气体排出，无论剂量或给药途径如何。在最低口服剂量下，72小时内回收了83%的放射性标记（51%在尿液中，12%在粪便中，17%作为呼出的14CO2，<1%作为呼出的[14C]柠檬醛，以及3%在总组织中）。14CO2的产生在处理后12小时基本停止，在任何组织中发现的14C量非常小（<2%）。随着口服剂量的增加，这种排泄轮廓没有太大变化，尽管在最低剂量下氧化成CO2的程度略高。

Male Fischer F344 rats were given citral labelled with 14C at the C1 and C2 positions in a single oral dose of 5, 50, or 500 mg/kg bw or an intravenous dose of 5 mg/kg bw. After 72 h, the animals were sacrificed and tissues and excreta analyzed for radioactivity. Most radiolabel was excreted in the urine, feces, and expired air as 14CO2 or [14C]citral within 24 hr, regardless of the dose or route of administration. At the lowest oral dose, 83% of the radiolabel was recovered within 72 hr (51% in urine, 12% in feces, 17% as expired 14CO2, <1% as expired [14C]citral, and 3% in total tissues). Production of 14CO2 essentially ceased 12 hr after treatment, and the amount of 14C found in any tissue was very small (<2%). This excretion profile did not change much with increasing oral dose, although ... oxidation to CO2 was somewhat greater at the lowest dose.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在大鼠和小鼠口服给药中，柠檬醛从胃肠道被迅速吸收，导致在12小时内小鼠全身均匀分布标记物。放射性物质被迅速排泄，主要途径是泌尿道。没有证据表明在体内有长期储存。

In rat & mouse orally admin citral was rapidly absorbed from gi tract, resulting in uniform distribution of label throughout body of mouse by 12 hr. Radioactivity was excreted rapidly, major route being urinary tract. No evidence for long-term storage in body.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在雄性Fischer大鼠中，研究了柠檬醛在静脉注射、口服和皮肤给药后的处置情况。静脉注射或口服暴露后，柠檬醛的分布和消除模式相同。尿液是柠檬醛放射性衍生物的主要消除途径，其次是粪便、二氧化碳和呼出的气体。然而，在皮肤暴露后，相对较少的物质通过尿液排出，更多的通过粪便排出，这表明皮肤首次通过代谢的作用。柠檬醛几乎完全通过口服吸收；由于其极高的挥发性，大量涂抹的皮肤剂量丢失。留在皮肤上的柠檬醛吸收得相当好。在5到500毫克/千克的口服剂量下，没有检测到对处置的影响。尽管粪便是一个次要的排泄途径，但大约25%的给药剂量在大鼠静脉注射后4小时内通过胆汁排出。柠檬醛的代谢既快速又广泛。在大鼠静脉注射后5分钟内，血液中检测不到未代谢的柠檬醛。重复暴露于柠檬醛导致胆汁排泄增加，而尿液、粪便或呼出的排泄模式没有显著变化。这表明柠檬醛可能诱导至少一条自身的代谢途径。这种化合物的快速代谢和排泄表明，柠檬醛不会显著生物累积。

The disposition of citral was studied in male Fischer rats after iv, po, and dermal treatments. The pattern of distribution and elimination was the same after iv or oral exposure. Urine was the major route of elimination of citral-derived radioactivity, followed by feces, (14)C02, and expired. However, after dermal exposure, relatively less of the material was eliminated in the urine and more in the feces, suggesting a role for first-pass metabolism through the skin. Citral was almost completely absorbed orally; due to its extreme volatility, much of an applied dermal dose was lost. The citral remaining on the skin was fairly well absorbed. No effect of oral dose, from 5 to 500 mg/kg, was detected on disposition. Although the feces was a minor route of excretion, approximately 25% of the administered dose was eliminated via the bile within 4 hr of an iv dose. The metabolism of citral was both rapid and extensive. Within 5 min of an iv dose, no unmetabolized citral could be detected in the blood. Repeated exposure to citral resulted in an increase in biliary elimination, without any significant change in the pattern of urinary, fecal, or exhaled excretion. This suggests that citral may induce at least one pathway of its own metabolism. The rapid metabolism and excretion of this compound suggest that significant bioaccumulation of citral would not occur.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  8
• 危险品标志：
  Xi
• 危险类别码：
  R38,R43
• 危险品运输编号：
  175kgs
• WGK Germany：
  1
• RTECS号：
  RG5075000
• 包装等级：
  III
• 危险类别：
  8
• 储存条件：
  | 20°C，惰性气体 |

制备方法与用途

生产方法如下：

1. 在硫酸的作用下能环化生成对异丙基甲苯，在强碱的作用下能树脂化。此外，它还容易发生氧化或还原反应。

2. 可从柠檬草油中分离得到，也可由香叶醇、橙花醇或芳樟醇经氧化而制得。

反应信息

• 作为反应物：
  描述：

  (E)-3,7-二甲基-2,6-辛二烯醛 在 吡啶 、 2,2,6,6-四甲基哌啶 、 正丁基锂 、 Cp*Rh(OAc)2 、 copper(II) acetate monohydrate 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 96.65h， 生成 番茄红素
  参考文献：
  名称：

  合成天然和人工萜类化合物的模块化方法

  摘要：

  一种稳健的chem-stamp方法由两个步骤组成，即醛的单碳延伸至烯基硼酸酯以及这些烯基硼酸酯与 2,3-联烯醇的铑催化反应，已被开发用于构建萜类化合物中的关键异戊二烯单元。这种方法可以通过控制异戊二烯单元、侧链和两个末端基团的数量，实现萜类化合物的模块化简明合成和人造萜类化合物的创建。

  DOI：

  10.1002/anie.202307626
• 作为产物：
  描述：

  芳樟醇 在 氢氧化钾 、 乙醚 、 三溴化磷 、 异丙醇 、 硝基环己烷 作用下， 生成 (E)-3,7-二甲基-2,6-辛二烯醛
  参考文献：
  名称：

  类胡萝卜素中的合成物。11.米特隆。α，β-Ungesättigteausylhalogeniden mityls Nitroparaffinen †

  摘要：

  从利那洛尔开始，柠檬醛是通过使香叶基卤化物与硝基石蜡的碱金属盐反应制得的。通过相同的方法，获得了其他α，β-不饱和羰基化合物，它们是合成类胡萝卜素的有用中间体。

  DOI：

  10.1002/hlca.19570400516
• 作为试剂：
  描述：

  苯甲醛 、 (二甲基苯硅烷基)硼酸频那醇酯 在 甲醇 、 (E)-3,7-二甲基-2,6-辛二烯醛 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以39%的产率得到(dimethyl(phenyl)silyl)(phenyl)methanol
  参考文献：
  名称：

  铜催化将亲核硅添加到醛中

  摘要：

  如何训练硅烷：制备了带有双氟化抗衡阴离子的新的手性铜（I）配合物家族，并将其用于甲硅烷基对醛的对映选择性转移的第一个例子中。该方法可快速获得高对映选择性的非外消旋α-羟基硅烷。

  DOI：

  10.1002/anie.201209020

文献信息

• [EN] ENCAPSULATES<br/>[FR] PRODUITS ENCAPSULÉS
  申请人：PROCTER & GAMBLE

  公开号：WO2013022949A1

  公开（公告）日：2013-02-14

  The present application relates to encapsulates, compositions, products comprising such encapsulates, and processes for making and using such encapsulates. Such encapsulates comprise a core comprising a perfume and a shell that encapsulates said core, such encapsulates may optionally comprise a parametric balancing agent, such shell comprising one or more azobenzene moieties.

  本申请涉及封装体、组合物、包含这种封装体的产品，以及制备和使用这种封装体的方法。这种封装体包括一个包含香水的核心和封装该核心的壳，这种封装体可以选择性地包含一个参数平衡剂，该壳包括一个或多个偶氮苯基团。
• Wet THF as a Suitable Solvent for a Mild and Convenient Reduction of Carbonyl Compounds with NaBH₄
  作者：Behzad Zeynizadeh、Tarifeh Behyar

  DOI：10.1246/bcsj.78.307

  日期：2005.2

  NaBH 4 in wet THF can readily reduce varieties of carbonyl compounds such as aldehydes, ketones, conjugated enones, acyloins, and α-diketones to their corresponding alcohols in good to excellent yields. Reduction reactions were performed at room temperature or under reflux condition. In addition, the chemoselective reduction of aldehydes over ketones was accomplished successfully with this reducing

  湿 THF 中的 NaBH 4 可以很容易地将各种羰基化合物还原为相应的醇，例如醛、酮、共轭烯酮、酰基和 α-二酮，收率非常好。还原反应在室温或回流条件下进行。此外，使用该还原系统成功地完成了醛相对于酮的化学选择性还原。
• Modified Hydroborate Agent: (2,2′-Bipyridyl)(tetrahydroborato)zinc Complex, [Zn(BH₄)₂(bpy)], as a New, Stable, Efficient Ligand-Metal Hydroborate and Chemoselective Reducing Agent
  作者：Behzad Zeynizadeh

  DOI：10.1246/bcsj.76.317

  日期：2003.2

  rato)zinc complex, [Zn(BH4)2(bpy)], is a new white stable compound which has been used for efficient reduction of variety of carbonyl compounds such as aldehydes, ketones, acyloins, α-diketones and α,β-unsaturated carbonyl compounds (1,2-reduction) to their corresponding alcohols in acetonitrile at room temperature. Excellent chemoselectivity was also observed for the reduction of aldehydes over ketones

  (2,2'-联吡啶基)(四氢硼酸根)锌配合物，[Zn(BH4)2(bpy)]，是一种新型白色稳定化合物，已用于有效还原各种羰基化合物，如醛、酮、酰基化合物, α-二酮和 α,β-不饱和羰基化合物（1,2-还原）在乙腈中在室温下转化为相应的醇。还观察到使用这种还原剂还原醛而不是酮具有优异的化学选择性。
• NaBH₄/NaHSO₄·H₂O a Heterogeneous Acidic System for a Mild and Convenient Reduction of Carbonyl Compounds under Protic Condition
  作者：Behzad Zeynizadeh、Tarifeh Behyar

  DOI：10.1515/znb-2005-0417

  日期：2005.4.1

  NaBH₄ in the presence of sodium bisulfate (NaHSO₄·H₂O), a weakly acidic reagent, efficiently reduces a variety of carbonyl compounds such as aldehydes, ketones, α,β -unsaturated aldehydes and ketones, α-diketones and acyloins to their corresponding alcohols in acetonitrile under heterogeneous condition. Reduction reactions were accomplished at room temperature or under reflux condition

  NaBH₄在存在硫酸氢钠（NaHSO₄·H₂O）的情况下，作为一种弱酸试剂，能够高效地将各种羰基化合物如醛、酮、α,β-不饱和醛和酮、α-二酮和酰基酮在乙腈中在非均相条件下还原为它们相应的醇。还原反应可在室温或回流条件下完成。
• Some uses of mischmetall in organic synthesis
  作者：Marie-Isabelle Lannou、Florence Hélion、Jean-Louis Namy

  DOI：10.1016/j.tet.2003.07.017

  日期：2003.12

  Mischmetall, an alloy of the light lanthanides, has been used in a variety of organic reactions, either as a coreductant in samarium(II)-mediated reactions (Barbier and Grignard-type reactions, pinacolic coupling reactions) or as the promoter of Reformatsky-type reactions. It has been also employed as the starting material for easy syntheses of lanthanide trihalides, the reactivity of which has been

  Mischmetall是一种轻型镧系元素的合金，已用于多种有机反应中，作为sa（II）介导的反应（巴比尔和格利雅德型反应，松香偶联反应）的共轭物或Reformatsky-的促进剂。类型反应。它也被用作容易合成镧系三卤化物的起始原料，在今元和Luche-Fukuzawa反应以及Mukaiyama aldol反应中已经探究了其反应活性。

表征谱图